2,3-Bis-(4-chlor-phenyl)-acrylnitril | 3695-94-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,3-Bis-(4-chlor-phenyl)-acrylnitril
• 英文别名: 1,2-Bis-(4-chlor-phenyl)-1-cyan-ethylen；2,3-Bis(4-chlorophenyl)prop-2-enenitrile
• CAS: 3695-94-1
• 化学式: C₁₅H₉Cl₂N
• 分子量: 274.149
• InChiKey: YWNTXOMZGAMPDE-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  402.5±40.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-Bis-(4-chlor-phenyl)-acrylnitril 在 甲醇 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 生成 2,3-双(4-氯苯基)丙腈
  参考文献：
  名称：

  Amiel-Levy, Mazal; Hoz, Shmaryahu, Journal of the American Chemical Society, 2009, vol. 131, p. 8280 - 8284

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯苯甲醛 、 对氯苯乙腈 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以90%的产率得到2,3-Bis-(4-chlor-phenyl)-acrylnitril
  参考文献：
  名称：

  A Paal–Knorr Approach to 3,4-Diaryl-Substituted Pyrroles: Facile Synthesis of Lamellarins O and Q

  摘要：

  A very simple, yet efficient synthetic methodology, to obtain 3,4-diaryl-substituted pyrroles is described. The approach is based on the Knoevenagel condensation between arylacetonitriles and substituted aromatic aldehydes, followed by conjugate addition of cyanide to afford succinonitriles in excellent yields. The products thus obtained were subjected to DIBAL-H reduction, followed by cyclization under acidic conditions to produce the corresponding pyrroles in good overall yields. The utility of this protocol is exemplified by the synthesis of the marine alkaloids lamellarins O and Q.

  DOI：

  10.1055/s-0032-1317351

文献信息

• Catalytic Enantioselective Formal Synthesis of MDM2 Antagonist RG7388 and Its Analogues
  作者：Xue‐Jie Zou、Wu‐Lin Yang、Jing‐Yan Zhu、Wei‐Ping Deng

  DOI：10.1002/cjoc.201900530

  日期：2020.5

  The catalytic asymmetric 1,3‐dipolar [3 + 2] cycloaddition of azomethine ylides with stilbenes has been established, affording structurally diverse pyrrolidines bearing four contiguous stereocenters with stereo‐diversity in generally high yields and good to excellent stereoselectivities (up to 98% yield, 99 : 1 dr, >99% ee). Meanwhile, this strategy allowed the formal synthesis of antitumor drug RG7388

  已建立了甲亚胺烷基化物与对苯二甲酸酯的催化不对称1,3-偶极[3 + 2]环加成反应，从而提供了结构多样的吡咯烷，带有四个连续的立体中心，立体中心具有高收率，并且具有良好的优异立体选择性（高达98％的收率） ，99：1 dr，> 99％ee）。同时，该策略允许高效合成抗肿瘤药物RG7388（III期临床研究）。
• One-Pot Highly Stereoselective Synthesis of Cyano Aziridines via the CuCl-Catalyzed Aminochlorination of α,β-Unsaturated Nitriles and Intramolecular SN2 Substitution
  作者：Haibo Mei、Lijun Yan、Jianlin Han、Guigen Li、Yi Pan

  DOI：10.1111/j.1747-0285.2010.01023.x

  日期：2010.11

  An efficient one‐pot system has been developed for the synthesis of cyano aziridine by using α,β‐unsaturated nitriles as the alkene substrates and N,N‐dichloro‐p‐toluenesulfonamide (4‐TsNCl2) as the nitrogen source. A good scope of alkene substrates was achieved for this reaction. The one‐pot reaction, via aminohalogenation and intramolecular SN2 substitution, was very convenient to carry out at room temperature without the protection of inert gases. Modest to good yields and excellent have been obtained. This method provides an easy route to the cyano aziridine. The structure of the resulting products has been unambiguously confirmed by X‐ray structural analysis.